As a qualitative study and that employs teacher research methods and activity theory analysis, this dissertation explores the effectiveness of an assignment designed to both teach introductory technical and business communication students how to better write for nonacademic (workplace) audiences and to facilitate skills and knowledge transfer using Wikipedia as a writing medium. In particular, it explores the potential and problems that can arise when contradiction, something that can interfere with an individual's successful completion of a task, is used to promote student learning. In a three-article format, the author presents case studies of one technical communication student and three business communication students and narrates the surprises and struggles of researching and writing a dissertation in which the data leads in a direction other than her original intention. The first article presents the narrative of Penni17, a chemical engineering student enrolled in introductory technical communication, whose anxiety over the assignment ultimately revealed a contradiction between the student's and instructor's perceptions and interpretations of the instructor's learning goals and interfered with the student's learning. The second article presents the narratives of three business communication students who similarly misunderstood their instructors' learning goals, the terminology he used to describe their tasks, and his purpose in using Wikipedia as a medium. For these students and the majority of their classmates, the contradictions that arose contributed to their lack of motivation to work on the assignment and inhibited their learning. However, when one student was able to negotiate the contradiction she faced with another's help, her learning progressed. The third article is a teacher-research narrative that presents the author's own struggles to keep the dissertation focused on audience (and what students learned about vii writing for audience) rather than on learning and contradiction, and concludes that teaching audience is much more complicated than the professional communication field has previously acknowledged or treated it. The author argues for a more expansive (less isolated, or situated) view of audience than that which currently exists within the field. Ultimately, the author argues for an approach to teaching audience that complicates students' notions of audience and introduces the deliberate use and concept of contradiction in the classroom to promote student learning. All of the interest in Aristotle's Rhetoric had served to put the focus of rhetoric and composition scholars on the concept of audience. Inevitably, however, scholars would point out that there was a problem with using the Rhetoric as a model for a modern concept of audience or method of audience analysis. The Rhetoric was "a rhetoric for speech occasions" (Porter, 1992, p. 21), which differed tremendously from writers' circumstances. While audience analysis could be useful for determining how to tailor information for audienc...